Synthetic Studies on Polysaccharide HS-142-1, a Novel Nonpeptide Antagonist for the Atrial Natriuretic Peptide Receptor: Syntheses of the Gentiobiosyl Fragments | Zendy

Yi Qiu | Zendy; Yoshiaki Nakahara | Zendy; Tomoya Ogawa | Zendy

Open Access

Synthetic Studies on Polysaccharide HS-142-1, a Novel Nonpeptide Antagonist for the Atrial Natriuretic Peptide Receptor: Syntheses of the Gentiobiosyl Fragments

Author(s) -

Yi Qiu,

Yoshiaki Nakahara,

Tomoya Ogawa

Publication year - 1996

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.60.986

Subject(s) - polysaccharide , pyranose , chemistry , disaccharide , stereochemistry , derivative (finance) , antagonist , receptor , peptide , atrial natriuretic peptide , biochemistry , biology , endocrinology , financial economics , economics

Possible disaccharide fragments of the major component of HS-142-1, a novel polysaccharide antagonist for functional atrial natriuretic peptide (ANP) receptors, O-(4-O-caproyl-beta-D-glucopyranosyl)-(1 --> 6)-4-O-caproyl-D-glucopyranose (1) and O-(3-O-caproyl-beta-D-glucopyranosyl)-(1 --> 6)-3-O-caproyl-D-glucopyranose (2), were respectively synthesized in a stereo- and regio-controlled manner. Deprotection of 2,2'-di-O-caproyl derivative 35 gave a complex mixture due to undesired acyl migration. In contrast, 2,4'-di-O-caproyl analog 39 was successfully deprotected to give O-(4-O-caproyl-beta-D-glucopyranosyl)-(1 --> 6)-2-O-caproyl-D-glucopyranose (40).

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